Cas no 130930-25-5 (Z-cis-D-4-Hydroxyproline)

Z-cis-D-4-Hydroxyproline is a non-proteinogenic amino acid derivative characterized by its unique cis-configuration and hydroxylation at the 4-position of the proline ring. This stereochemically distinct compound serves as a valuable chiral building block in peptide synthesis and medicinal chemistry, enabling precise structural modifications to enhance peptide stability and bioactivity. Its hydroxyl group offers additional functionalization sites for conjugation or derivatization, making it useful in drug design and biochemical research. The Z-configuration further provides steric constraints that influence peptide secondary structure, aiding in the study of conformation-activity relationships. High-purity grades ensure reproducibility in research applications.
Z-cis-D-4-Hydroxyproline structure
Z-cis-D-4-Hydroxyproline structure
Product Name:Z-cis-D-4-Hydroxyproline
CAS No:130930-25-5
MF:C13H15NO5
MW:265.261904001236
MDL:MFCD03428474
CID:91673
PubChem ID:688416
Update Time:2025-05-20

Z-cis-D-4-Hydroxyproline Chemical and Physical Properties

Names and Identifiers

    • Z-D-CIS-HYP-OH
    • (2R,4R)-N-ALPHA-CARBOBENZOXY-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC-ACID
    • N-ALPHA-CARBOBENZOXY-CIS-4-HYDROXY-D-PROLINE
    • (2s,4s)-N-carbobenzyloxy-4-hydroxy-L-proline
    • (2R,4R)-1-(Benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
    • (2R,4R)-Carbobenzoxy-4-hydroxypyrrolidine-2-carboxylic-acid
    • Z-D-HYP-OH
    • (2R,3R)-pinobanksin
    • (2R,3S)-3-phenyloxirane-2-carboxamide
    • (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
    • 2R,3R-3,5,7-trihydroxy flavanone
    • 2R,3S-(-)-3-phenylglycidamide
    • 2R,3S-3-phenyloxirane-2-carboxami
    • 2R,4R-1-Benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid
    • 3,5,7-Trihydroxyflavanone
    • AC1Q6KIT
    • Arbo 15
    • cis-1-benzyloxycarbonyl-4-hydroxy-D-proline
    • N-benzyloxycarbonyl-cis-4-hydroxy-D-proline
    • pinobanksin
    • (2S,4S)-1-(Benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
    • (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
    • EN300-6942352
    • (2R,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
    • 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(phenylmethyl) ester, (2R,4R)-
    • FD21768
    • WWVCWLBEARZMAH-GHMZBOCLSA-N
    • MFCD03428474
    • SCHEMBL28269
    • AS-49198
    • Z-CIS-HYP-OH
    • AMY6607
    • N-CBZ-CIS-4-HYDROXY-D-PROLINE
    • (2R,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
    • 130930-25-5
    • cis4-hydroxy-N-benzyloxycarbonyl-D-proline
    • AKOS017511674
    • 1,2-Pyrrolidinedicarboxylicacid,4-hydroxy-,1-(phenylmethyl)ester,(2S,4S)-
    • (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylicacid
    • Z-cis-D-4-Hydroxyproline
    • MDL: MFCD03428474
    • Inchi: 1S/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10-,11-/m1/s1
    • InChI Key: WWVCWLBEARZMAH-GHMZBOCLSA-N
    • SMILES: O[C@H]1CN(C(=O)OCC2C=CC=CC=2)[C@@H](C(=O)O)C1

Computed Properties

  • Exact Mass: 265.09500
  • Monoisotopic Mass: 265.09502258g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 5
  • Complexity: 340
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.8
  • Topological Polar Surface Area: 87.1?2

Experimental Properties

  • Density: 1.416
  • Boiling Point: 486.9°C at 760 mmHg
  • Flash Point: 248.3°C
  • Refractive Index: 1.612
  • PSA: 87.07000
  • LogP: 0.78090

Z-cis-D-4-Hydroxyproline Pricemore >>

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Z-cis-D-4-Hydroxyproline Production Method

Z-cis-D-4-Hydroxyproline Suppliers

Amadis Chemical Company Limited
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(CAS:130930-25-5)Z-cis-D-4-Hydroxyproline
Order Number:A1120180
Stock Status:in Stock
Quantity:5g
Purity:99%
Pricing Information Last Updated:Thursday, 29 August 2024 21:24
Price ($):216.0

Additional information on Z-cis-D-4-Hydroxyproline

Z-cis-D-4-Hydroxyproline: A Comprehensive Overview

Z-cis-D-4-Hydroxyproline, also known by its CAS number 130930-25-5, is a naturally occurring amino acid derivative that has garnered significant attention in the fields of biochemistry and pharmacology. This compound is a hydroxylated derivative of proline, a non-essential amino acid, and plays a crucial role in various biological processes. The Z-cis configuration refers to the stereochemistry of the molecule, which is essential for its biological activity. Recent studies have highlighted its potential in therapeutic applications, particularly in the context of tissue repair and regeneration.

The chemical structure of Z-cis-D-4-Hydroxyproline is characterized by a hydroxyl group (-OH) attached to the fourth carbon of the proline ring. This modification imparts unique properties to the molecule, enabling it to participate in hydrogen bonding and other molecular interactions that are critical for its function. The D designation indicates that the compound is in its dextrorotatory form, which is the biologically active enantiomer. Researchers have found that this stereochemistry is vital for its interaction with cellular components, such as enzymes and receptors.

Recent advancements in biochemical research have shed light on the role of Z-cis-D-4-Hydroxyproline in collagen synthesis. Collagen is a key structural protein found in connective tissues, and its proper formation is essential for maintaining tissue integrity. Studies have demonstrated that this compound acts as a cofactor in the hydroxylation of proline residues during collagen synthesis, a process that stabilizes the triple-helical structure of collagen fibers. This stabilization enhances the mechanical properties of connective tissues, making Z-cis-D-4-Hydroxyproline a promising candidate for treating conditions such as wounds, burns, and degenerative diseases.

In addition to its role in collagen synthesis, Z-cis-D-4-Hydroxyproline has been implicated in modulating cellular signaling pathways. Recent research has shown that this compound can influence the activity of matrix metalloproteinases (MMPs), enzymes that play a dual role in tissue remodeling by degrading extracellular matrix components. By regulating MMP activity, Z-cis-D-4-Hydroxyproline may help maintain a balance between tissue degradation and repair, which is critical in pathological conditions such as fibrosis and cancer.

The potential therapeutic applications of Z-cis-D-4-Hydroxyproline are vast and continue to be explored. One area of interest is its use in wound healing therapies. Preclinical studies have demonstrated that topical application of this compound can accelerate wound closure by enhancing collagen deposition and reducing inflammation. Furthermore, its ability to modulate cellular signaling pathways suggests its potential utility in treating chronic wounds, which are often resistant to conventional therapies.

Another promising avenue for Z-cis-D-4-Hydroxyproline is its application in anti-aging skincare products. Collagen degradation is a hallmark of skin aging, leading to wrinkles and loss of elasticity. By promoting collagen synthesis and stabilizing its structure, this compound may help mitigate these effects and restore youthful skin appearance. Recent clinical trials have shown encouraging results, with participants experiencing improved skin texture and reduced wrinkle depth after using products containing Z-cis-D-4-Hydroxyproline.

Despite its numerous potential benefits, further research is needed to fully understand the mechanisms underlying Z-cis-D-4-Hydroxyproline's biological effects. Long-term safety studies are essential to ensure that this compound can be used safely over extended periods without adverse effects. Additionally, exploring its interactions with other biomolecules could uncover new therapeutic applications or synergistic effects when combined with other compounds.

In conclusion, Z-cis-D-4-Hydroxyproline (CAS No. 130930-25-5) is a versatile compound with significant potential in various biomedical applications. Its role in collagen synthesis, modulation of cellular signaling pathways, and therapeutic benefits make it an exciting area of research. As ongoing studies continue to unravel its mechanisms and applications, Z-cis-D-4-Hydroxyproline holds promise as a valuable tool in advancing treatments for tissue repair, skin aging, and beyond.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:130930-25-5)Z-cis-D-4-Hydroxyproline
A1120180
Purity:99%
Quantity:5g
Price ($):216.0
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